Ligand Modification for Selectivity Control in Selective Ethylene Oligomerization

Yun Ah Kim; Seong Jin Oh; Seowon Cho; Kyung-sun Son

Macromolecular Research, Vol.26, No.4, 341-345, April, 2018

DOI10.1007/s13233-018-6044-9 Export Citation

Ligand Modification for Selectivity Control in Selective Ethylene Oligomerization

Yun Ah Kim, Seong Jin Oh, Seowon Cho, and Kyung-sun Son^†

Department of Chemistry, Chungnam National University, Daejeon 34134, Korea

E-mail:

A series of aminophosphine ligands were synthesized by in situ combination of CrCl3(THF)3 and dry methylaluminoxane and examined for their catalytic behavior in chromium-catalyzed selective ethylene oligomerization. Variations of the ligand scaffold obtained by modifying the diarylphosphine moiety affected the steric bulkiness, which resulted in remarkable changes in the selectivity for 1-hexene vs. 1-octene. Based on our experimental results, we evaluated two different mechanisms proposed for selective ethylene oligomerization.

Keywords:ethylene oligomerization;α-olefin;homogeneous catalysis;chromium

[References]

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Despite the development of selective oligomerization systems, there is considerable debate concerning the mechanistic details, such as the discrimination between seven-, nine-membered vs. larger rings.
Zhang J, Wang X, Zhang X, Wu W, Zhang G, Xu S, Shi M, ACS Catal., 3, 2311 (2013)
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Zhang L, Meng X, Chen Y, Cao C, Jiang T, ChemCatChem, 9, 76 (2017)
Kim EH, Lee HM, Jeong MS, Ryu JY, Lee J, Lee BY, ACS Omega, 2, 765 (2017)
Peitz S, Aluri BR, Peulecke N, Muller BH, Wohl A, Muller W, Al-Hazmi MH, Mosa FM, Rosenthal U, Chemistry, 16, 7670 (2010)
Carter A, Cohen SA, Cooley NA, Murphy A, Scutt J, Wass DF, Chem. Commun., 858 (2002).
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The direct characterization of the catalytically active species was unsuccessful due to the paramagnetic nature of the chromium complexes.

[1] Agapie T, Coord. Chem. Rev., 255, 861 (2011)

[2] McGuinness DS, Chem. Rev., 111(3), 2321 (2011)

[3] Alferov KA, Belov GP, Meng YZ, Appl. Catal. A: Gen., 542, 71 (2017)

[4] Overett MJ, Blann K, Bollmann A, Dixon JT, Hess F, Killian E, Maumela H, Morgan DH, Neveling A, Otto S, Chem. Commun., 622 (2005).

[5] Sydora OL, Jones TC, Small BL, Nett AJ, Fischer AA, Carney MJ, ACS Catal., 2, 2452 (2012)

[6] Cloete N, Visser HG, Engelbrecht I, Overett MJ, Gabrielli WF, Roodt A, Inorg. Chem., 52(5), 2268 (2013)

[7] Sa S, Lee SM, Kim SY, J. Mol. Catal. A-Chem., 378, 17 (2013)

[8] Do LH, Labinger JA, Bercaw JE, ACS Catal., 3, 2582 (2013)

[9] Manyik RM, Walker WE, Wilson TP, J. Catal., 47, 197 (1977)

[10] Briggs JR, J. Chem. Soc., Chem. Commun., 674 (1989).

[11] Wass DF, Dalton Trans., 816 (2007).

[12] Emrich R, Heinemann O, Jolly PW, Kruger C, Verhovnik GPJ, Organometallics, 16, 1511 (1997)

[13] Agapie T, Schofer SJ, Labinger JA, Bercaw JE, J. Am. Chem. Soc., 126(5), 1304 (2004)

[14] McGuinness DS, Suttil JA, Gardiner MG, Davies NW, Organometallics, 27, 4238 (2008)

[15] Yang Y, Liu Z, Cheng R, He X, Liu B, Organometallics, 33, 2599 (2014)

[16] Overett MJ, Blann K, Bollmann A, Dixon JT, Haasbroek D, Killian E, Maumela H, McGuinness DS, Morgan DH, J. Am. Chem. Soc., 127(30), 10723 (2005)

[17] Despite the development of selective oligomerization systems, there is considerable debate concerning the mechanistic details, such as the discrimination between seven-, nine-membered vs. larger rings.

[18] Zhang J, Wang X, Zhang X, Wu W, Zhang G, Xu S, Shi M, ACS Catal., 3, 2311 (2013)

[19] Stennett TE, Haddow MF, Wass DF, Organometallics, 31, 6960 (2012)

[20] Dixon JT, Green MJ, Hess FM, Morgan DH, J. Organomet. Chem., 689, 3641 (2004)

[21] Bollmann A, Blann K, Dixon JT, Hess FM, Killian E, Maumela H, McGuinness DS, Morgan DH, Neveling A, Otto S, Overett M, Slawin AMZ, Wasserscheid P, Kuhlmann S, J. Am. Chem. Soc., 126(45), 14712 (2004)

[22] Kim SK, Kim TJ, Chung JH, Hahn TK, Chae SS, Lee HS, Cheong M, Kang SO, Organometallics, 29, 5805 (2010)

[23] Licciulli S, Thapa I, Albahily K, Korobkov I, Gambarotta S, Duchateau R, Chevalier R, Schuhen K, Angew. Chem.-Int. Edit., 49, 9225 (2010)

[24] Dulai A, McMullin CL, Tenza K, Wass DF, Organometallics, 30, 935 (2011)

[25] Shaikh Y, Albahily K, Sutcliffe M, Fomitcheva V, Gambarotta S, Korobkov I, Duchateau R, Angew. Chem.-Int. Edit., 51, 1366 (2012)

[26] Shaikh Y, Gurnham J, Albahily K, Gambarotta S, Korobkov I, Organometallics, 31, 7427 (2012)

[27] Sattler A, Aluthge DC, Winkler JR, Labinger JA, Bercaw JE, ACS Catal., 6, 19 (2016)

[28] Zhang L, Meng X, Chen Y, Cao C, Jiang T, ChemCatChem, 9, 76 (2017)

[29] Kim EH, Lee HM, Jeong MS, Ryu JY, Lee J, Lee BY, ACS Omega, 2, 765 (2017)

[30] Peitz S, Aluri BR, Peulecke N, Muller BH, Wohl A, Muller W, Al-Hazmi MH, Mosa FM, Rosenthal U, Chemistry, 16, 7670 (2010)

[31] Carter A, Cohen SA, Cooley NA, Murphy A, Scutt J, Wass DF, Chem. Commun., 858 (2002).

[32] Blann K, Bollmann A, Dixon JT, Hess FM, Killian E, Maumela H, Morgan DH, Neveling A, Otto S, Overett MJ, Chem. Commun., 620 (2005).

[33] Agapie T, Day MW, Henling LM, Labinger JA, Bercaw JE, Organometallics, 25, 2733 (2006)

[34] The direct characterization of the catalytically active species was unsuccessful due to the paramagnetic nature of the chromium complexes.